CO2作为化学品原料的高效利用途径: 与烷烃耦合反应

doi:10.1016/S1872-2067(23)64416-X

催化学报 ›› 2023, Vol. 47: 138-149.DOI: 10.1016/S1872-2067(23)64416-X

CO₂作为化学品原料的高效利用途径: 与烷烃耦合反应

危长城^a^,^b, 张雯娜^a, 杨阔^a^,^c, 柏秀^a^,^d, 徐舒涛^a, 李金哲^a,*(), 刘中民^a^,^b,*()

^a中国科学院大连化学物理研究所, 洁净能源国家实验室, 低碳催化技术国家工程研究中心, 辽宁大连116023
^b中国科学院大学, 北京100049
^c大连理工大学化工学院催化化学与工程系, 精细化工国家重点实验室, 辽宁大连116024
^d大连理工大学张大煜化学学院, 辽宁大连116024

收稿日期:2023-02-13 接受日期:2023-02-16 出版日期:2023-04-18 发布日期:2023-03-20
通讯作者: *电子信箱: lijinzhe@dicp.ac.cn (李金哲),liuzm@dicp.ac.cn (刘中民).
基金资助:
国家自然科学基金(21991093);国家自然科学基金(21991090);国家自然科学基金(22288101)

An efficient way to use CO₂ as chemical feedstock by coupling with alkanes

Changcheng Wei^a^,^b, Wenna Zhang^a, Kuo Yang^a^,^c, Xiu Bai^a^,^d, Shutao Xu^a, Jinzhe Li^a,*(), Zhongmin Liu^a^,^b,*()

^aNational Engineering Research Center of Lower-Carbon Catalysis Technology, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China
^cState Key Laboratory of Fine Chemicals, Department of Catalysis Chemistry and Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China
^dZhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024, Liaoning, China

Received:2023-02-13 Accepted:2023-02-16 Online:2023-04-18 Published:2023-03-20
Contact: *E-mail: lijinzhe@dicp.ac.cn (J. Li),liuzm@dicp.ac.cn (Z. Liu).
Supported by:
National Natural Science Foundation of China(21991093);National Natural Science Foundation of China(21991090);National Natural Science Foundation of China(22288101)

摘要/Abstract

摘要：

CO₂作为碳资源的规模化高附加值利用是实现其减排的重要方向. 然而, 由于其热力学稳定, 以CO₂为原料高效转化为大宗化学品一直是一个巨大的挑战. 工业上普遍以富氢的石脑油为原料生产相对缺氢的烯烃和芳烃产品, 但其存在原料和目标产品之间的碳氢不平衡问题. 理论上, 采用CO₂与富氢的烷烃耦合, 可以改善二者的平衡关系, 提高目标产物选择性, 同时实现CO₂资源化利用. 已有研究采用CO₂与烷烃反应, 将CO₂转化为CO并减少氢气的生成, 但CO₂的碳原子没有进入烃类产物中. 本文系统研究了酸性分子筛催化的CO₂与烷烃耦合反应, 大幅提高了芳烃选择性, 证实部分CO₂中的碳原子直接进入了芳烃产品中.

本文以H-ZSM-5为催化剂, 对比研究了正丁烷、正戊烷和正己烷在He和CO₂气氛中的转化反应, 并详细研究了反应温度、CO₂/n-butane比例、接触时间以及分子筛酸量等条件对耦合反应的影响. 结果表明, CO₂的引入可大幅促进芳烃的生成, 同时甲烷和乙烷等小分子烷烃的生成受到抑制. 在优化反应条件下, CO₂/n-butane比例为0.475时, CO₂和n-butane转化率分别可达17.5%和100%, 芳烃选择性高达80%. 使用¹³C同位素标记的CO₂与n-butane进行耦合反应, 发现芳烃产物中含有部分¹³C同位素标记的碳原子, 表明这部分碳原子来自CO₂中的碳. 对耦合反应后的催化剂进行溶积碳并采用色质谱分析, 发现大量甲基取代的内酯和甲基取代的环烯酮等含氧物种. 同位素标记实验结果表明, 这些含氧中间体由CO₂与烃类耦合转化生成. 通过设计实验验证了反应途径, 即CO₂与碳正离子反应得到环内酯, 环内酯进一步转化为甲基环烯酮, 甲基环烯酮转化为芳烃产物. 提出了H-ZSM-5催化CO₂与烷烃耦合反应的机理, 并采用密度泛函理论计算了耦合反应机理各步骤的能垒, 结果验证了耦合反应机理的可行性. 综上, 本文提出的耦合反应为CO₂碳资源的大规模直接利用提供了一条有效的途径, 具有广阔的应用前景.

关键词: 二氧化碳转化, 轻质烷烃, 芳烃, 催化, 分子筛

Abstract:

The most promising method to eliminate CO₂ is to find large-scale and value-added applications of CO₂as a carbon resource. However, the utilization of CO₂ as feedstock for basic chemicals has long been a great challenge owing to its high thermodynamic stability. Herein, we report the coupling conversion of CO₂ with light alkanes over the HZSM-5 zeolite with much higher aromatic selectivity than light alkanes as the only reactant. A CO₂ conversion of 17.5% and n-butane conversion of 100% with aromatic selectivity of 80% could be achieved by the coupling reaction at the CO₂ to n-butane ratio of 0.475, in which CO₂ not only acted as an agent for balancing hydrogen in the reaction but also partly (~25%) incorporated into the aromatic products. Methyl-substituted lactones (MLTOs) and methyl-substituted cycloalkenones (MCEOs) were identified as key intermediates during the coupling reaction. ¹³C isotope labeling experiments, ¹³C solid-state NMR, in-situ diffuse reflectance infrared Fourier transform spectroscopy, and density functional theory (DFT)calculations revealed that CO₂could react with carbonium ions generated from alkane cracking to form MLTOs, which could further get converted into MCEOs, thus generating aromatic compounds. This coupling reaction provides guidance for the direct utilization of CO₂ to produce value-added chemicals with the simultaneous transformation of light alkanes.

Key words: CO₂ utilization, Light alkanes, Aromatics, Catalysis, Zeolite

危长城, 张雯娜, 杨阔, 柏秀, 徐舒涛, 李金哲, 刘中民. CO₂作为化学品原料的高效利用途径: 与烷烃耦合反应[J]. 催化学报, 2023, 47: 138-149.

Changcheng Wei, Wenna Zhang, Kuo Yang, Xiu Bai, Shutao Xu, Jinzhe Li, Zhongmin Liu. An efficient way to use CO₂ as chemical feedstock by coupling with alkanes[J]. Chinese Journal of Catalysis, 2023, 47: 138-149.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(23)64416-X

https://www.cjcatal.com/CN/Y2023/V47/I4/138

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Fig. 1. Catalytic performance of light alkanes conversion in CO2 or He. (a) Comparison of alkane conversion and the product distribution for the conversion of n-butane, n-pentane, and n-hexane in He or CO2. Reaction conditions: 0.4 g HZSM-5(17), T = 500 °C, Pn-alkane = 21 kPa, in CO2 (PCO2 = 2355 kPa and PAr = 124 kPa) or He (PHe = 2479 kPa), total flow = 30 mL/min at standard temperature and pressure (STP), time on stream (TOS) = 2.4 h. (b) Catalytic performance of n-butane conversion in CO2 or He plotted as a function of TOS. Detailed comparison of aromatics (c) and C1?C3 alkanes (d) selectivity. Others are mainly composed of C4+ alkanes, and A9+ aromatics includes ethylbenzene and the aromatics with more than eight carbon atoms. The amount of hydrogen in the products was very small (< 0.5 wt%) and the carbon balance was calculated about 97% for the reactions.

Fig. 2. Effects of reaction conditions on the coupling reaction of n-butane with CO2 over HZSM-5. Effects of CO2 partial pressure on the coupling reaction: (a) n-butane conversion and products selectivity; (b) C1?C3 alkane selectivity, the molar ratio of converted CO2 to converted n-butane and (H/C)hydrocarbons ratios. Reaction conditions: 0.4 g HZSM-5(17), T = 450 °C, Pn-butane = 13 kPa, PCO2 = 454?2355 kPa and PAr = 33?124 kPa, total flow = 10-48 mL/min at STP, TOS = 2.4 h. (c) Effects of reaction temperature on the coupling reaction. Reaction conditions: 0.4 g HZSM-5(17), Pn-butane = 31 kPa, PCO2 = 2346 kPa and PAr = 123 kPa, total flow = 20 mL/min at STP, TOS = 2.4 h. (d) Effects of contact time on the coupling reaction. Reaction conditions: 0.02-0.8 g HZSM-5(17), T = 500 °C, Pn-butane = 31 kPa, PCO2 = 2346 kPa and PAr = 123 kPa, total flow = 20 mL/min at STP, TOS = 2.4 h. (e) Catalytic performance of coupling reaction at relative low ratio of CO2 to n-butane. Reaction conditions: 1.2 g HZSM-5(17), T = 550 °C, P = 2500 kPa, PCO2/Pn-butane/PAr = 1.9/0.4/0.1, 1.9/1/0.1, 1.9/2/0.1 and 1.9/4/0.1, total flow = 30 mL/min at STP, TOS = 2.1 h. (f) Optimization of CO2 conversion plotted as a function of TOS. Reaction conditions: 1.2 g HZSM-5(17), T = 550 °C, Pn-butane = 1667 kPa, PCO2 = 792 kPa and PAr = 42 kPa, total flow = 30 mL/min at STP. Others are mainly composed of C4+ alkanes, and A9+ aromatics includes ethylbenzene and the aromatic products with more than eight carbon atoms.

Fig. 3. Effects of the Al/(Si+Al) ratio of HZSM-5 on the coupling reaction of n-butane with CO2. Products selectivity (a) and conversion and (H/C)hydrocarbons ratios (b). Reaction conditions: 0.4 g catalyst, T = 500 °C, Pn-butane = 31 kPa, PCO2 = 2346 kPa and PAr = 123 kPa, total flow = 20 mL/min at STP, TOS = 2.4 h. Others are mainly composed of C4+ alkanes.

Fig. 4. (a) 13C distribution of representative products in the effluent during the coupling reaction of n-butane with 13CO2. Contrast of MS spectra of toluene (b) and p-xylene (c) in the effluent during the coupling reaction of n-butane with 13CO2 (up) and 12CO2 (bottom) over HZSM-5. Reaction conditions: 0.2 g HZSM-5(17), T = 450 °C, Pn-butane = 4 kPa, PHe = 162 kPa, PCO2 = 333 kPa, total flow = 9 mL/min at STP.

Fig. 5. GC-MS analysis of retained species occluded in spent HZSM-5(17). (a) GC-MS results (retention times of up to 18 min) of the retained species occluded in spent zeolite after the coupling reaction at 250 °C. (b) Peak area of MCEOs relative to that of internal standard at different temperatures; (c) 13C distribution of oxygenated compounds occluded in spent zeolite after the coupling reaction of n-butane with 13CO2. Reaction conditions: 0.2 g HZSM-5(17), T = 200 and 450 °C, Pn-butane = 4 kPa, PHe = 162 kPa, PCO2 = 333 kPa, total flow = 9 mL/min at STP, and the catalyst was removed after the coupling reaction for 1 h.

Fig. 6. (a) GC-MS results for the retained species occluded in HZSM-5(17) after GVL conversion at different temperature. (b) In situ UV-vis spectra recorded during GVL conversion. (c,d) Gas chromatogram of products in the effluent during GVL conversion over HZSM-5(17) at different temperature: (c) chromatogram results detected by FID; (d) chromatogram results detected by TCD. Reaction conditions: 0.2 g HZSM-5(17), carrier gas (He) = 30 mL/min at STP, WHSV = 1 h?1, TOS = 0.8 h. (e) Peak area ratio of butadiene to CO (black) and butene to CO2 (red) in GC spectra of GVL conversion. Reaction conditions: 0.1 g HZSM-5(17), T = 400 °C, carrier gas (He) = 20 mL/min at STP, WHSV = 1.3 h?1.

Fig. 7. (a) GC-MS results of retained species occluded in spent HZSM-5(17) after the conversion of propene in CO2 or He atmosphere. Reaction conditions: 0.2 g HZSM-5(17), T = 200 °C, Ppropene = 1.8 kPa, PCO2 or PHe = 360 kPa, total flow = 22 mL/min at STP. The catalysts were removed after 5 min of reaction. 13C MAS NMR spectra of HZSM-5(17) on the co-reaction of propene with 13CO (b) or 12CO (c) at different temperatures.

Fig. 9. Proposed mechanism of the aromatic formation (Route A) and CO formation (Route B) for the coupling conversion of n-butane and CO2 over HZSM-5. The calculated free energy barriers of all the elementary reactions (at 450 °C) are given in kJ/mol.

Fig. 8. In situ DRIFT spectra recorded during n-butane conversion in CO2 (a) or Ar (b) atmosphere.

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CO₂作为化学品原料的高效利用途径: 与烷烃耦合反应

An efficient way to use CO₂ as chemical feedstock by coupling with alkanes

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